CHIRP

Debug log uploaded

Ok, if I see that right, then it works sometimes, and sometimes it fails during write?
The errors I saw vary from "Failed to communicate with the radio: write failed: (9, 'Bad file descriptor')" to "Failed to communicate with the radio: Attempting to use a port that is not open". My best guess is trouble with the USB driver - which wouldn't be a surprise with the operating system you're using.

Does any of these documents help?
CableGuide
CableGuide FTDI OEM Cables
RTSystemsCablesAndMavericks

Tried everything in the wiki guides. No luck. Where i was once able to upload to Chirp, I cannot even do that now. Tried going back to a previous setting and that didn't work either. Im not the most computer literate person so I'm lost.

Unfortunately I'm not a Mac user myself. Hopefully someone with experience on USB to Serial converters under MacOS can give some advice here?

Some MacOS notes: this OS is apparently very picky about USB to Serial cables. From what I heard, only (genuine) FTDI-based cables can be made work.
You also must have the KK7DS Python runtime for Mac OSX installed.

Any luck?
There's another Wiki article which could help: MacOS Tips.